SL Letter of the Day: Only the Lonely

I'm on hiatus while working on a manuscript for a new book. In the meantime, please enjoy these classic Savage Love letters pulled from previous columns. I will be back November 1st, when the book is finished. —Dan

This question comes from a point of real frustration. I'm a 26-year-old straight guy. Due to my being overweight, awkward, and generally unable to attract women I'm actually interested in, I have only been sexually intimate with prostitutes and women of low caliber. I have never been able to sustain an erection during intercourse. I've climaxed during oral sex or handjobs. I'm not physically accustomed to getting off with anything but my hand. Worst of all, the intense fear of impotence has caused me to avoid sexual liaisons. When dating, I feel threatened by the expectation of sex within the first few dates. Any solid advice?

Sick Of Beatin'

My response after the jump...

Join a gym and lose some weight. You'll gain some confidence and improve your health—and your circulation—which could help in the keeping-the-dick-hard department. (I'm not telling you that you have to transform yourself into a muscle god to be happy or find love.) Seeing a doctor and getting your hands on some Viagra couldn't hurt, either. Vary your masturbatory technique.

Stop sleeping with women unless you're attracted to them on some level, and recognize that holding the women who will sleep with you in contempt is an expression of self-hatred and knock it the fuck off. Since sex within the first few dates makes you feel anxious, inform anyone you date that you're not up for having sex within the first few dates. And the next time you find yourself in bed with someone or sense that things are headed there, SOB, tell her that you're really only interested in oral and mutual masturbation—at least at first—and that you generally take a long time to come. Then you don't have to stress out about failing to meet her expectations, because she won't be expecting anything other than what you're capable of delivering.

Finally, there are sex workers out there who will not only get you off in exchange for your money, SOB, but will work with you on improving your skills and building up your confidence. You may have slept with one already without realizing it because you so resented having to pay for it that you dismissed her as a cheap whore to protect your ego. Dumb mistake.